U.S. patent application number 12/002118 was filed with the patent office on 2008-06-19 for ink-jet recording ink.
This patent application is currently assigned to Seiko Epson Corporation. Invention is credited to Masahiro Yatake.
Application Number | 20080146712 12/002118 |
Document ID | / |
Family ID | 39528233 |
Filed Date | 2008-06-19 |
United States Patent
Application |
20080146712 |
Kind Code |
A1 |
Yatake; Masahiro |
June 19, 2008 |
Ink-jet recording ink
Abstract
An inkjet recording ink comprising water, a pigment, a
dispersion polymer, and the compound of Formula 1, wherein said
dispersion polymer has 50 wt % or more of benzyl acrylate and 15 wt
% or less of (meth)acrylic acid as components, and has an acid
value of at least 50 mg KOH/g but not more than 120 mg KOH/g and a
weight-average molecular weight of at least 20,000 but not more
than 120,000: R--POn-EOm-HFormula 1 (wherein, R is an alkanol group
with 8 to 18 carbon atoms, PO is a propyleneoxy group, EO is an
ethyleneoxy group, H is hydrogen, n is a number from 4 to 12, m is
a number from 1 to 12, and PO and EO may be random or blocks).
Inventors: |
Yatake; Masahiro;
(Shiejiri-shi, JP) |
Correspondence
Address: |
Edwards Angell Palmer & Dodge LLP
P.O. Box 55874
Boston
MA
02205
US
|
Assignee: |
Seiko Epson Corporation
Tokyo
JP
|
Family ID: |
39528233 |
Appl. No.: |
12/002118 |
Filed: |
December 13, 2007 |
Current U.S.
Class: |
524/376 |
Current CPC
Class: |
C09D 11/326
20130101 |
Class at
Publication: |
524/376 |
International
Class: |
C09D 11/10 20060101
C09D011/10 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 14, 2006 |
JP |
2006-336674 |
Claims
1. An inkjet recording ink comprising water, a pigment, a
dispersion polymer, and the compound of Formula 1, wherein said
dispersion polymer has 50 wt % or more of benzyl acrylate and 15 wt
% or less of (meth)acrylic acid as components, and has an acid
value of at least 50 mg KOH/g but not more than 120 mg KOH/g and a
weight-average molecular weight of at least 20,000 but not more
than 120,000: R--POn-EOm-H Formula 1 (wherein, R is an alkanol
group with 8 to 18 carbon atoms, PO is a propyleneoxy group, EO is
an ethyleneoxy group, H is hydrogen, n is a number from 4 to 12, m
is a number from 1 to 12, and PO and EO may be random or
blocks).
2. The inkjet recording ink according to claim 1, comprising at
least 0.05 wt % but not more than 1 wt % of one or more selected
from 2,4,7,9-tetramethyl-5-decyn-4,7-diol and an
2,4,7,9-tetramethyl-5-decyn-4,7-diol alkylene oxide addition
product.
3. The inkjet recording ink according to claim 1, comprising
1,2-alkylene glycol.
4. The inkjet recording ink according to claim 1, comprising one or
more selected from di(tri)ethylene glycol monobutyl ether and
(di)propylene glycol monobutyl ether.
5. The inkjet recording ink according to claim 1, comprising
2-butyl-2-ethyl-1,3-propanediol.
Description
[0001] The entire disclosure of Japanese Patent Application No.
2006-336674 filed on Dec. 14, 2006 is expressly incorporated by
reference herein.
BACKGROUND
[0002] 1. Technical Field
[0003] The present invention relates to an inkjet recording ink
excellent in storage stability and discharge stability and also
having strong color development on plain paper and glossy paper as
well as high glossiness on glossy paper.
[0004] 2. Related Art
[0005] Existing inkjet recording inks commonly use dyes as the
coloring material, but those using pigments are becoming more
popular. In the case of inks using pigments, methods that have been
examined for dispersing the pigments in water include methods using
surfactants (JP-A-1-301760), methods of dispersal using a
dispersion polymer having a hydrophobic part and a hydrophilic part
(JP-B-5-064724), and methods in which the surface of the pigment is
coated with a polymer, such as for example methods using
phase-inversion emulsification or acid precipitation
(JP-A-10-140065).
SUMMARY
[0006] However, because a polymer having styrene as a principal
component was used for dispersing the pigment in all cases,
fixation was poor and the printed matter tended to turn yellow
during long-term storage. Moreover, under normal circumstances if a
surfactant, glycol ether or other substance having a hydrophilic
part and a hydrophobic part is present in the ink the polymer
becomes more liable to adsorption and desorption, thus degrading
the storage stability of the ink. With existing aqueous ink, a
surfactant, glycol ether or other substance having a hydrophilic
part and a hydrophobic part is required in order to reduce blurring
of the ink on paper. Inks that lack such substances do not permeate
the paper sufficiently, the types of papers on which uniform
printing can be performed are limited, and the printed image tends
to degrade.
[0007] The problem with adding an additive for improving printing
quality (acetylene glycol, acetylene alcohol, silicon-based
surfactant, di(tri)ethylene glycol monobutyl ether or 1,2-alkylene
glycol or a mixture of these) for example to an existing pigment
dispersion is that long-term storage stability cannot be obtained,
and in the case of a pigment ink, because of its poor redissolution
properties the ink tends to clog the nozzle of the inkjet head upon
drying and attack the adhesives and other materials used to make up
the head, thereby detracting from adhesive strength and discharge
stability.
[0008] Other problems that have occurred when pigments are
dispersed in such a common dispersants are that dispersant residue
remains in the ink system or the dispersant becomes separated from
the pigment without contributing sufficiently to dispersal,
resulting in increased viscosity. Increased viscosity restricts the
amount of pigment other coloring material that can be added, and
adequate printing quality may not be obtained, especially on plain
paper.
[0009] An inkjet recording ink according to an aspect of the
invention contains water, a pigment dispersed using a polymer
having a weight-average molecular weight of at least 20,000 but not
more than 120,000 and an acid value of at least 50 mg KOH/g but not
more than 120 mg KOH/g which is obtained by polymerizing at least
50 wt % or more of benzyl acrylate and 15 wt % or less of
(meth)acrylic acid as polymer components, along with the compound
of Formula 1:
R--POn-EOm-H Formula 1
(wherein R is an alkanol group with 8 to 18 carbon atoms, PO is a
propyleneoxy group, EO is an ethyleneoxy group, H is hydrogen, n is
a number from 4 to 12, m is a number from 1 to 12, and PO and EO
may be random or blocks).
[0010] An inkjet recording ink according to an aspect of the
invention has the effect of providing an inkjet recording ink which
is excellent in storage stability and discharge stability and which
also has strong color development on plain paper and glossy paper
as well as high glossiness on glossy paper.
DESCRIPTION OF EXEMPLARY EMBODIMENTS
[0011] Embodiments of the present invention are explained next. The
following embodiments are examples for explaining the present
invention and are not intended to limit the present invention. The
present invention can be embodied in various other ways as long as
the essence of the invention is not violated.
[0012] An inkjet recording ink according to an aspect of the
invention is the result of exhaustive research in light of demand
for such properties as excellent storage stability and discharge
stability, strong color development on plain paper and glossy
paper, adequate glossiness and fixation on glossy paper and
excellent discharge stability of the ink from the inkjet head.
[0013] An inkjet recording ink according to an aspect of the
invention contains water, a pigment dispersed using a polymer
having a weight-average molecular weight of at least 20,000 but not
more than 120,000 and an acid value of at least 50 mg KOH/g but not
more than 120 mg KOH/g which is obtained by polymerizing at least
50 wt % or more of benzyl acrylate and 15 wt % or less of
(meth)acrylic acid as polymer components, along with the compound
of Formula 1. If the acid value is below 50 mg KOH/g dispersion
stability will not be obtained, while if it exceeds 120 mg KOH/g
color development on plain paper will decline. If the
weight-average molecular weight is less than 20,000 the long-term
storage stability, thermal stability and fixation of the inkjet ink
will be adversely affected, while if it exceeds 120,000 the inkjet
ink will be more viscous, tending to detract from dispersion
stability as well as from discharge stability. Moreover, if the
alkyl alcohol polyoxypropylene and polyoxyethylene addition product
has fewer than 8 carbon atoms glossiness will be less on glossy
paper, while if it has more than 16 the ink will be more viscous
and discharge stability will not be obtained.
[0014] According to another aspect of the invention, R in the
compound of Formula 1 is preferably an alkanol group with 8 to 16
carbon atoms. If the number of carbon atoms is less than 8 it will
be difficult to obtain glossiness on glossy paper. If it exceeds
16, solubility in water is increased, and it will be necessary to
add more ethyleneoxy groups, increasing the risk of bubbling and
therefore of inkjet dot skip, and also detracting from color
development on plain paper. n is preferably 4 to 12 because below 4
it is hard to improve glossiness on glossy paper, while above 12
solubility in water is increased and it is necessary to add more
ethyleneoxy groups, increasing the risk of bubbling and therefore
of inkjet dot skip, and also detracting from color development on
plain paper. m is 1 to 12 because below 1 solubility in water is
poor, limiting the amount that can be added so that glossiness
cannot be obtained on glossy paper. Above 12 bubbling is more
likely, increasing the risk of inkjet dot skip and detracting from
color development on plain paper. The propyleneoxy and ethyleneoxy
groups may be added to the alkyl group either randomly or in
blocks, but a structure produced by first adding the propyleneoxy
groups as blocks to the alkyl group and then adding the ethyleneoxy
groups as blocks results in better glossiness on glossy paper and
better color development on plain paper than random addition or
addition of the ethyleneoxy groups as blocks followed by addition
of the ethyleneoxy groups as blocks the alkyl group.
[0015] According to one aspect of the invention, it is desirable to
polymerize 50 wt % or more of benzyl acrylate and 15 wt % or less
of (meth)acrylic acid as the polymer components, and the preferred
range of benzyl acrylate here is 50 wt % or more because fixation
declines below 50 wt %, but amounts below 50 wt % are not excluded.
Consequently, 50 wt % or more is desirable but 60 wt % or more is
more desirable and 70 wt % or more is still more desirable.
Polymerization with 15 wt % or less of (meth)acrylic acid is also
desirable because above 15 wt % the color development of the inkjet
ink tends to be poorer on plain paper, but amounts above 15 wt %
are not excluded, and a more desirable range is 10 wt % or less.
Comparing methacrylic acid and acrylic acid, moreover, acrylic acid
is preferred from the standpoint of fixation.
[0016] Examples of the pigment used in an aspect of the present
invention include furnace black, lamp black, acetylene black,
channel black and other forms of carbon black (C.I. pigment black
7) and copper oxides, iron oxides (C.I. pigment black 11), titanium
oxide and other metals and aniline black (C.I. pigment black 1) and
other organic pigments for example in the case of black ink, but
carbon black is preferred for inkjet use because it has a
relatively low specific density and does not tend to precipitate in
water. Examples of color pigments include C.I. pigment yellow 1
(fast yellow G), 3, 12 (disazo yellow AAA), 13, 14, 17, 24, 34, 35,
37, 42 (yellow iron oxide), 53, 55, 74, 81, 83 (disazo yellow HR),
93, 94, 95, 97, 98, 100, 101, 104, 108, 109, 110, 117, 120, 128,
138, 153 and 180, C.I. pigment red 1, 2, 3, 5, 17, 22 (brilliant
fast scarlet), 23, 31, 38, 48:2 (permanent red 2B (Ba)), 48:2
(permanent red 2B (Ca)), 48:3 (permanent red 2B (Sr)), 48:4
(permanent red 2B (Mn)), 49:1, 52:2, 53:1, 57:1 (brilliant carmine
6B), 60:1, 63:1, 63:2, 64:1, 81 (rhodamine 6G lake), 83, 88, 101
(red iron oxide), 104, 105, 106, 108 (cadmium red), 112, 114, 122
(quinacridone magenta), 123, 146, 149, 166, 168, 170, 172, 177,
178, 179, 185, 190, 193, 209 and 219, C.I. pigment blue 1, 2, 15
(phthalocyanine blue R), 15:1, 15:2, 15:3 (phthalocyanine blue G),
15:4, 15:6 (phthalocyanine blue E), 16, 17:1, 56, 60 and 63, and
C.I. pigment green 1, 4, 7, 8, 10, 17, 18 and 36 and the like.
[0017] According to an aspect of the present invention the added
amount of the pigment is preferably 0.5% to 30% or more preferably
1.0% to 12%. Below this the printing concentration cannot be
maintained, while if more than this is added the ink will be more
viscous and will acquire structural viscosity, which tends to
detract from discharge stability of the ink from the inkjet
head.
[0018] When such an inkjet recording ink prepared with such a
pigment uses a pigment other than yellow, such as C.I. black 7,
C.I. pigment blue 15:1, C.I. pigment blue 15:2, C.I. pigment blue
15:3, C.I. pigment blue 15:4, C.I. pigment blue 15:6, C.I. pigment
green 36, C.I. pigment red 122, C.I. pigment red 177, C.I. pigment
red 254, C.I. pigment violet 19 or C.I. pigment violet 23, it is
desirable from the standpoint of providing an inkjet recording ink
with excellent storage stability and discharge stability which also
has strong color development on plain and glossy paper and high
glossiness on glossy paper that the pigment be dispersed using a
polymer having an average particle diameter of 90 nm or less and an
acid value of at least 50 mg KOH/g but not more than 100 mg KOH/g.
If the average particle diameter is over 90 nm, glossiness on
glossy paper will be reduced. Dispersal will be unstable if the
acid value is below 50 mg KOH/g. If the acid value exceeds 100 mg
KOH/g, color development on plain paper will be reduced. More
preferably, the acid value is between 60 mg KOH/g and 100 mg
KOH/g.
[0019] When such an inkjet recording ink prepared with such a
pigment uses a yellow pigment such as C.I. pigment yellow 55, C.I.
pigment yellow 74, C.I. pigment yellow 79, C.I. pigment yellow 93,
C.I. pigment yellow 110, C.I. pigment yellow 120, C.I. pigment
yellow 128, C.I. pigment yellow 138, C.I. pigment yellow 139, C.I.
pigment yellow 150, C.I. pigment yellow 151, C.I. pigment yellow
155, C.I. pigment yellow 156, C.I. pigment yellow 175 or C.I.
pigment yellow 180, it is desirable from the standpoint of
providing an inkjet recording ink with excellent storage stability
and discharge stability which also has strong color development on
plain and glossy paper and high glossiness on glossy paper that the
pigment be dispersed using a polymer having an average particle
diameter of at least 20 nm but not more than 110 nm and an acid
value of at least 50 mg KOH/g but not more than 120 mg KOH/g. If
the average particle diameter is less than 20 nm light fastness
will be poor, while if it exceeds 110 nm color development on plain
paper will be reduced. If the acid value is below 50 mg KOH/g
dispersal will be unstable, while if it exceeds 120 mg KOH/g color
development on plain paper will be reduced.
[0020] One or more selected from the commercial
styrene-(meth)acrylic acid copolymers, styrene-(meth)acrylic
acid-(meth)acrylic acid ester copolymers, polyethylene glycol
(meth)acrylate-(meth)acrylic acid copolymers, vinyl acetate-maleic
acid copolymers, styrene-maleic acid copolymers and the like can be
combined in the polymer for dispersing the pigment in an aspect of
the present invention to the extent that the invention is not
affected. However, it is desirable that a copolymer of an acrylate
and acrylic acid constitute at least 80% of the polymer. A
commercial acrylate such as methyl acrylate, ethyl acrylate, propyl
acrylate, butyl acrylate, hexyl acrylate, cyclohexyl acrylate,
octyl acrylate, lauryl acrylate, 2-ethylhexyl acrylate,
2-ethylhexylcarbitol acrylate, phenol EO denatured acrylate,
N-vinylpyrrolidone, isobornyl acrylate, benzyl acrylate, paracumyl
phenol EO denatured acrylate, 2-hydroxyethyl-3-phenoxypropyl
acrylate or the like can be used as this acrylate.
.omega.-carboxy-polycaprolactone monoacrylate, monohydroxyethyl
phthalate acrylate, acrylic acid dimer or the like can also be used
in place of acrylic acid.
[0021] The dispersal method using a polymer in an aspect of the
invention is preferably phase inversion emulsification in water so
as to coat the pigment with the polymer. Phase inversion
emulsification stabilizes the ink and improves color development on
plain paper.
[0022] Less than 0.05 wt % of one or more selected from
2,4,7,9-tetramethyl-5-decyn-4,7-diol,
3,6-dimethyl-4-octyl-3,6-diol, 2,4,7,9-tetramethyl-5-decyn-4,7-diol
alkylene oxide addition product and 3,6-dimethyl-4-octyl-3,6-diol
alkylene oxide addition product is undesirable because there will
be more blurring on plain paper. Above 1 wt % the inkjet ink will
have poor storage stability, making long-term storage difficult.
The preferred range is therefore at least 0.1 wt % but not more
than 0.7 wt %.
[0023] 2,4,7,9-tetramethyl-5-decyn-4,7-diol,
3,6-dimethyl-4-octyl-3,6-diol and
2,4,7,9-tetramethyl-5-decyn-4,7-diol alkylene oxide addition
product are commercially available, and can be obtained for example
as Nisshin Chemical Surfinol 104, Surfinol 82, Surfinol 2502,
Surfinol 420, Surfinol 440, Surfinol 465, Surfinol 485 and Kawaken
Fine Chemicals Acetylenol EOO, Acetylenol E40, Acetylenol E100 and
the like.
[0024] It is desirable to include a 1,2-alkylene glycol in one
aspect of the invention. Of the 1,2-alkylene glycols,
1,2-hexanediol and 4-methyl-1,2-pentanediol are particularly
desirable, and the discharge stability of the inkjet ink is
improved and blurring is reduced when printing on plain paper when
these are used in addition to a pigment of an aspect of the present
invention.
[0025] It is also desirable to include one or more selected from
di(tri)ethylene glycol monobutyl ether, (di)propylene glycol
monobutyl ether, di(tri)ethylene glycol monopentyl ether and
di(tri)ethylene glycol monohexyl ether. Bleeding is further reduced
and printing quality is improved when printing on plain paper in an
inkjet system when these glycol ethers are used in addition to a
pigment of an aspect of the present invention.
[0026] It is also desirable to include
2-butyl-2-ethyl-1,3-propanediol, and glossiness on glossy paper and
color development on plain paper are improved when
2-butyl-2-ethyl-1,3-propanediol is used in addition to a pigment of
an aspect of the present invention.
[0027] A polymer in an aspect of the invention has carboxyl groups,
and triethanolamine and/or tripropanolamine are preferably included
as counter-ions. Clogging by the inkjet ink is unlikely to occur
even when the ink dries if triethanolamine and/or tripropanolamine
are included.
[0028] Likewise, one or more selected from glycerin,
trimethylolethane, trimethylolpropane and the tetrasaccharides,
pentasaccharides and hexasaccharides is preferably included in
order to reduce the risk of clogging by the inkjet ink.
[0029] An alcohol solvent, ketone solvent, ether solvent or glycol
ether solvent can be used as the solvent in the method of
polymerizing the polymer in an aspect of the present invention.
However, because the pigment will be dispersed in a water system
this solvent must be one that can be subsequently removed. The
following can be used as such solvents. Examples of such alcohol
solvents include methanol, ethanol, isopropanol, 1-butanol,
tertiary butanol, isobutanol, diacetone alcohol and the like.
Examples of such ketone solvents include acetone, methyl ethyl
ketone, diethyl ketone, methyl isobutyl ketone, cyclohexanone and
the like. Examples of such ether solvents include dibutyl ether,
tetrahydrofuran, dioxane and the like. Examples of such glycol
ethers include ethylene glycol monomethyl ether, diethylene glycol
monomethyl ether, diethylene glycol monoethyl ether, diethylene
glycol diethyl ether, butyl cellosolve and the like.
[0030] The radical polymerization initiator used to polymerize the
polymer can be an organic peroxide such as t-butyl
peroxy(2-ethylhexanoate), di-t-butyl peroxide, t-butyl
peroxybenzoate or t-butyl peroxyoctoate, an azo compound such as
2,2'-azobisisobutyronitrile,
2,2'-azobis(2,4-dimethylvaleronitrile),
dimethyl-2,2'-azobisbutyrate, 2,2'-azobis(2-methylbutyronitrile) or
the like, or potassium persulfate, sodium persulfate or the like,
but is not limited to these, and another initiator can be used as
long as it is capable of radical polymerization. The radical
polymerization initiator is preferably used in the amount of at
least 0.01 mol % but not more than 5 mol % of the monomers used
during polymerization. The polymerization temperature in this case
is not particularly limited but is normally in the range of
30.degree. C. to 100.degree. C. or preferably 40.degree. C. to
90.degree. C. If the polymerization temperature is too low too much
time may be required to polymerize the monomers, and in some cases
the polymerization rate may decline, resulting in large quantities
of residual monomers.
[0031] Dispersants, surface tension adjusters or isotonic agents
(surfactants), humidity anti-drying agents, preservatives,
antibacterial agents, pH adjusters, rustproofing agents, humectants
and other additives can be used as necessary in aspects of the
present invention. These may be used alone, or 2 or more may be
used in combination.
[0032] Methods of manufacturing an inkjet ink according to an
aspect of the invention include for example a method in which the
polymer composition for the inkjet ink of this aspect is emulsified
by high-speed agitation together with an aqueous solvent and an
alkali such as sodium hydroxide or the like, and the pigment and
the like are then added and forcibly dispersed with a disperser or
the like. If necessary, it is also possible to use a method of
dispersal with a triple-roll mill, after which the resulting
pigment slurry is dispersed with a high-pressure disperser or the
like until a specific particle diameter is achieved, and the
organic solvent and the like are then removed from the resulting
pigment dispersion.
[0033] The high-pressure disperser is not particularly limited, and
may for example be a Microfluidizer (Microfluidics Co.), Altemizer
(Sugino Machine), wet-jet mill (Genus Co.), Nanomizer (S.G.
Engineering) or the like.
[0034] The pressure for dispersing with this high-pressure
disperser may be any that achieves the desired pigment particle
diameter, but is preferably 100 MPa to 300 MPa. Below 100 MPa the
dispersed particle diameter may be too large, dispersal may take
too much time, or it may be difficult to obtain a stable dispersal
without an extremely large number of passes, which is uneconomical.
Above 300 MPa overdispersal is likely, and a stable dispersion will
probably not be obtained. When the desired pigment particle
diameter cannot be achieved, the number of dispersals can be
increased or the pressure can be raised within the pressure range
described above.
[0035] An inkjet ink polymer composition that is obtained by adding
an alkali solution to the aforementioned inkjet ink polymer
composition after polymerization, heating it, and removing the
solvent and replacing it with ion-exchange water can also be used
in a method of manufacturing an inkjet ink of one aspect of the
present invention.
[0036] It is also possible to use an inkjet ink polymer solution
obtained by removing the solvent by vacuum distillation from the
aforementioned inkjet ink polymer after polymerization, pulverizing
the resulting inkjet ink polymer solids, and adding and heating
ion-exchange water, alkali solution and the like to dissolve the
solids. In this case, it is unnecessary to remove any organic
solvent and the like from the resulting pigment dispersion
solution.
[0037] The alkali used in the aforementioned alkali solution may be
triethanolamine, tripropanolamine or another tertiary alkanolamine
or alkyl alkanolamine, or an inorganic salt such as sodium
hydroxide, potassium hydroxide, lithium hydroxide or the like for
example.
EXAMPLES
[0038] The present invention is explained in more detail below
using Examples, but the invention is not limited only to these
examples, and various changes are possible to the extent that they
do not violate the intent of the invention.
Example 1
[0039] Nitrogen was substituted inside a 2000 ml separable flask
equipped with an agitator, a circulating tube, a thermometer and a
drip funnel, and 200.0 parts wt of diethylene glycol monomethyl
ether were placed in the separable flask and heated to 80.degree.
C. with agitation. Next, 200.0 parts wt of diethylene glycol
monomethyl ether, 483.0 parts wt of benzyl acrylate, 50.4 parts wt
of acrylic acid and 4.8 parts wt of t-butylperoxy(2-ethylhexanoate)
were placed in the drip funnel, and dripped into the separable
flask over 4 hours at 80.degree. C. to perform the reaction. After
completion of dripping, this was maintained at 80.degree. C. for 1
hour, after which 0.8 parts wt of t-butylperoxy(2-ethylhexanoate)
were added and reacted for 1 hour at 80.degree. C. The diethylene
glycol monomethyl ether was then removed by vacuum distillation.
600.0 parts wt of methyl ethyl ketone was then added to obtain a
polymer composition solution with a 50% resin solids component.
When part of the polymer composition solution obtained in this way
was taken and dried for 1 hours at 105.degree. C. in an ignition
drier, the resulting polymer composition solids had an acid value
of 65 mg KOH/g and a weight-average molecular weight (WAMW) of
34,000.
[0040] Next, 3.0 parts wt of a 30% sodium hydroxide aqueous
solution were added to 120.0 parts wt of the polymer composition
solution prepared above and agitated for 5 minutes with a
high-speed disperser, and 480.0 parts wt of C.I. pigment blue 15:4
(Clariant Co.) were added and agitated for 1 hour with a high-speed
disperser to obtain a pigment dispersion slurry. This pigment
dispersion slurry was then dispersed 10 times continuously at 200
MPa with an ultrahigh pressure homogenizer (Microfluidizer, Mizuho
Industrial Co., Ltd.) to obtain a pigment dispersion solution.
[0041] Part of the methyl ethyl ketone and water were removed by
vacuum distillation with an evaporator from the resulting pigment
dispersion solution, which was then centrifuged with a centrifuge
(05P-21, Hitachi) for 30 minutes at 5000 rpm, after which
ion-exchange water was added to a pigment concentration of 15 wt %
to prepare the pigment dispersion. This was filtered under pressure
with a 2.5 .mu.m membrane filter (Advantech). The inkjet ink of ink
composition 1 was then prepared as shown in Tables 4 through 6. In
the compound of Formula 1, R was a nonanol group, n was 7 and m was
4.
Example 2
[0042] The inkjet ink of Composition Example 2 as shown in Tables 4
through 6 was prepared as in Example 1 except that 13.2 parts of
methacrylic acid and 36.5 parts wt of acrylic acid were used
instead of 50.4 parts wt of acrylic acid. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4. When part of
the polymer composition solution was taken and dried for 1 hour at
105.degree. C. in an ignition drier, the resulting inkjet ink
polymer composition solids had an acid value of 60 mg KOH/g and a
weight-average molecular weight of 32,000.
Example 3
[0043] The inkjet ink of Composition Example 3 as shown in Tables 4
through 6 was prepared as in Example 1 except that 42.6 parts wt of
acrylic acid were used instead of 50.4 parts wt of acrylic acid. In
the compound of Formula 1, R was a nonanol group, n was 7 and m was
4. When part of the polymer composition solution was taken and
dried for 1 hour at 105.degree. C. in an ignition drier, the
resulting inkjet ink polymer composition solids had an acid value
of 55 mg KOH/g and a weight-average molecular weight of 48,000.
Example 4
[0044] The inkjet ink of Composition Example 4 as shown in Tables 4
through 6 was prepared as in Example 1 except that 77.5 parts wt of
acrylic acid were used instead of 50.4 parts wt of acrylic acid. In
the compound of Formula 1, R was a nonanol group, n was 7 and m was
4. When part of the polymer composition solution was taken and
dried for 1 hour at 105.degree. C. in an ignition drier, the
resulting inkjet ink polymer composition solids had an acid value
of 100 mg KOH/g and a weight-average molecular weight of
29,000.
Example 5
[0045] The inkjet ink of Composition Example 4 as shown in Tables 4
through 6 was prepared as in Example 1 except that 93.0 parts wt of
acrylic acid were used instead of 50.4 parts wt of acrylic acid. In
the compound of Formula 1, R was a nonanol group, n was 7 and m was
4. When part of the polymer composition solution was taken and
dried for 1 hour at 105.degree. C. in an ignition drier, the
resulting inkjet ink polymer composition solids had an acid value
of 120 mg KOG/g and a weight-average molecular weight of
34,000.
Example 6
[0046] The inkjet ink of Composition Example 13 as shown in Tables
4 through 6 was prepared as in Example 1 except that Monarch 800
(C.I. PBk7: Cabot Corp.) was used instead of 480.0 parts wt of C.I.
pigment blue 15:4 with a pigment concentration of 25 wt %. In the
compound of Formula 1, R was a nonanol group, n was 9 and m was
4.
Example 7
[0047] The inkjet ink of Composition Example 14 as shown in Tables
4 through 6 was prepared as in Example 2 except that Monarch 800
(C.I. pigment black 7: Cabot Corp.) was used instead of 480.0 parts
wt of C.I. pigment blue 15:4 with a pigment concentration of 25 wt
%. In the compound of Formula 1, R was a decanol group, n was 6 and
m was 4.
Example 8
[0048] The inkjet ink of Composition Example 19 as shown in Tables
4 through 6 was prepared as in Example 1 except that 120.0 parts wt
of C.I. pigment violet 19 was substituted for the 120.0 parts wt of
C.I. pigment blue 15:4. In Formula 1, compound R was an undecanol
group, n was 4 and m was 7.
Example 9
[0049] The inkjet ink of Composition Example 20 as shown in Tables
4 through 6 was prepared as in Example 2 except that 120.0 parts wt
of C.I. pigment violet 19 were used instead of 120.0 parts wt of
C.I. pigment blue 15:4. In the compound of Formula 1, R was a
nonanol group, n was 7 and m was 4.
Example 10
[0050] The inkjet ink of Composition Example 25 as shown in Tables
4 through 6 was prepared as in Example 1 except that 120.0 parts wt
of C.I. pigment yellow 74 (Clariant Co.) were used instead of 120.0
parts wt of C.I. pigment blue 15:4. In the compound of Formula 1, R
was a nonanol group, n was 7 and m was 4.
Example 11
[0051] The inkjet ink of Composition Example 26 as shown in Tables
4 through 6 was prepared as in Example 2 except that 120.0 parts wt
of C.I. pigment yellow 74 (Clariant Co.) were used instead of 120.0
parts wt of C.I. pigment blue 15:4. In the compound of Formula 1, R
was a nonanol group, n was 7 and m was 4.
Example 12
[0052] The inkjet ink of Composition Example 31 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8, R was an octanol group and PO-EO were
added as blocks in that order, with n being 4 and m being 4.
Example 13
[0053] The inkjet ink of Composition Example 32 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8, R was a nonanol group and PO-EO were
added as blocks in that order, with n being 9 and m being 4.
Example 14
[0054] The inkjet ink of Composition Example 33 as shown in Table 3
was prepared as in Example 8 except that instead of R being a
nonanol group, n being 7 and m being 4 in the compound of Formula 1
as in Example 8, R was a nonanol group and PO-EO were added as
blocks in that order, with n being 6 and m being 5.
Example 15
[0055] The inkjet ink of Composition Example 34 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8, R was an undecanol group and PO-EO were
added as blocks in that order, with n being 5 and m being 6.
Example 16
[0056] The inkjet ink of Composition Example 35 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8, R was a dodecanol group and PO-EO were
added as blocks in that order, with n being 4 and m being 6.
Example 17
[0057] The inkjet ink of Composition Example 36 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8, R was a nonanol group and PO-EO were
added as blocks in that order, with n being 7 and m being 4, and PO
and EO were randomly added.
Example 18
[0058] The inkjet ink of Composition Example 37 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8, R was a nonanol group and EO-PO were
added as blocks in that order, with n being 3 and m being 4.
Example 19
[0059] The inkjet ink of Composition Example 38 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8; R was a nonanol group and EO-PO were
added as blocks in that order, with n being 4 and m being 7.
Example 20
[0060] The inkjet ink of Composition Example 39 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of R
being a nonanol group, n being 7 and m being 4 in the compound of
Formula 1 as in Example 8, R was a decanol group and PO-EO were
added as blocks in that order, with n being 7 and m being 6, and PO
and EO were randomly added.
Comparative Example 1
[0061] The inkjet ink of Composition Example 6 as shown in Tables 4
through 6 was prepared as in Example 1 except that 100.8 parts wt
of acrylic acid were used instead of 50.4 parts wt of acrylic acid.
In the compound of Formula 1, R was a nonanol group, n was 7 and m
was 4. When part of the polymer composition solution was taken and
dried for 1 hour in an ignition dryer at 105.degree. C., the
resulting inkjet ink polymer composition solids had an acid value
of 130 mg KOH/g and a weight-average molecular weight of
29,000.
Comparative Example 2
[0062] The inkjet ink of Composition Example 7 as shown in Tables 4
through 6 was prepared as in Example 1 except that 116.3 parts wt
of acrylic acid were used instead of 50.4 parts wt of acrylic acid.
In the compound of Formula 1, R was a nonanol group, n was 7 and m
was 4. When part of the polymer composition solution was taken and
dried for 1 hour in an ignition dryer at 105.degree. C., the
resulting inkjet ink polymer composition solids had an acid value
of 150 mg KOH/g and a weight-average molecular weight of
34,000.
Comparative Example 3
[0063] The inkjet ink of Composition Example 8 as shown in Tables 4
through 6 was prepared as in Example 1 except that 155.0 parts wt
of acrylic acid were used instead of 50.4 parts wt of acrylic acid.
In the compound of Formula 1, R was a nonanol group, n was 7 and m
was 4. When part of the polymer composition solution was taken and
dried for 1 hour in an ignition dryer at 105.degree. C., the
resulting inkjet ink polymer composition solids had an acid value
of 200 mg KOH/g and a weight-average molecular weight of
29,000.
Comparative Example 4
[0064] The inkjet ink of Composition Example 9 as shown in Tables 4
through 6 was prepared as in Example 1 except that 20.0 parts wt of
t-butylperoxy(2-ethylhexanoate) were used instead of 4.8 parts wt
of t-butylperoxy(2-ethylhexanoate). In Formula 1, compound R was a
nonanol group, n was 7 and m was 4. When part of the polymer
composition solution was taken and dried for 1 hour in an ignition
dryer at 105.degree. C., the resulting inkjet ink polymer
composition solids had an acid value of 65 mg KOH/g and a
weight-average molecular weight of 10,000.
Comparative Example 5
[0065] The inkjet ink of Composition Example 10 as shown in Tables
4 through 6 was prepared as in Example 2 except that 15.0 parts wt
of t-butylperoxy(2-ethylhexanoate) were used instead of 4.8 parts
wt of t-butylperoxy(2-ethylhexanoate). In the compound of Formula
1, R was a nonanol group, n was 7 and m was 4. When part of the
polymer composition solution was taken and dried for 1 hour in an
ignition dryer at 105.degree. C., the resulting inkjet ink polymer
composition solids had an acid value of 60 mg KOH/g and a
weight-average molecular weight of 18,000.
Comparative Example 6
[0066] The inkjet ink of Composition Example 11 as shown in Tables
4 through 6 was prepared as in Example 1 except that 3.1 parts wt
of t-butylperoxy(2-ethylhexanoate) were used instead of 4.8 parts
wt of t-butylperoxy(2-ethylhexanoate). In the compound of Formula
1, R was a nonanol group, n was 7 and m was 4. When part of the
polymer composition solution was taken and dried for 1 hour in an
ignition dryer at 105.degree. C., the resulting inkjet ink polymer
composition solids had an acid value of 65 mg KOH/g and a
weight-average molecular weight of 140,000.
Comparative Example 7
[0067] The inkjet ink of Composition Example 12 as shown in Tables
4 through 6 was prepared as in Example 1 except that 23.3 parts wt
of acrylic acid were used rather than 50.4 parts wt of acrylic
acid. In the compound of Formula 1, R was an octanol group, n was 4
and m was 4. When part of the polymer composition solution was
taken and dried for 1 hour in an ignition dryer at 105.degree. C.,
the resulting inkjet ink polymer composition solids had an acid
value of 30 mg KOH/g and a weight-average molecular weight of
33,000.
Comparative Example 8
[0068] The inkjet ink of Composition Example 15 as shown in Tables
4 through 6 was prepared as in Comparative Example 1 except that
the 480.0 parts wt of C. I. pigment blue 15:4 were replaced with
480.0 parts wt of Monarch 800 (C.I. PBk7: Cabot Corp.). In the
compound of Formula 1, R was an undecanol group, n was 5 and m was
6.
Comparative Example 9
[0069] The inkjet ink of Composition Example 16 as shown in Tables
4 through 6 was prepared as in Comparative Example 5 except that
the 480.0 parts wt of C.I. pigment blue 15:4 were replaced with
480.0 parts wt of Monarch 800 (C.I. PBk7: Cabot Corp.). In the
compound of Formula 1, R was a nonanol group, n was 7 and m was
4.
Comparative Example 10
[0070] The inkjet ink of Composition Example 17 as shown in Tables
4 through 6 was prepared as in Comparative Example 6 except that
the 480.0 parts wt of C. I. pigment blue 15:4 were replaced with
480.0 parts wt of Monarch 800 (C. I. PBk7: Cabot Co.). In the
compound of Formula 1, R was a decanol group n was 4 and m was
6.
Comparative Example 11
[0071] The inkjet ink of Composition Example 18 as shown in Tables
4 through 6 was prepared as in Comparative Example 7 except that
the 480.0 parts wt of C.I. pigment blue 15:4 were replaced with
480.0 parts wt of Monarch 800 (C.I. PBk7: Cabot Corp.). In the
compound of Formula 1, R was a nonanol group, n was 3 and m was
4.
Comparative Example 12
[0072] The inkjet ink of Composition Example 21 as shown in Tables
4 through 6 was prepared as in Comparative Example 1 except that
the 480.0 parts wt of C.I. pigment blue 15:4 were replaced with
480.0 parts wt of C.I. pigment violet 19. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 13
[0073] The inkjet ink of Composition Example 22 as shown in Tables
4 through 6 was prepared as in Comparative Example 5 except that
the 480.0 parts wt of C. I. pigment blue 15:4 were replaced with
480.0 parts wt of C. I. pigment violet 19. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 14
[0074] The inkjet ink of Composition Example 23 as shown in Tables
4 through 6 was prepared as in Comparative Example 6 except that
the 480.0 parts wt of C.I. pigment blue 15:4 were replaced with
480.0 parts wt of C.I. pigment violet 19. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 15
[0075] The inkjet ink of Composition Example 24 as shown in Tables
4 through 6 was prepared as in Comparative Example 7 except that
the 480.0 parts wt of C.I. pigment blue 15:4 were replaced with
480.0 parts wt of C.I. pigment violet 19. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 16
[0076] The inkjet ink of Composition Example 27 as shown in Tables
4 through 6 was prepared as in Comparative Example 1 except that
the 480.0 parts wt of C. I. pigment blue 15:4 were replaced with
480.0 parts wt of C. I. pigment yellow 74. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 17
[0077] The inkjet ink of Composition Example 28 as shown in Tables
4 through 6 was prepared as in Comparative Example 5 except that
the 480.0 parts wt of C.I. pigment blue 15:4 were replaced with
480.0 parts wt of C.I. pigment yellow 74. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 18
[0078] The inkjet ink of Composition Example 29 as shown in Tables
4 through 6 was prepared as in Comparative Example 6 except that
the 480.0 parts wt of C.I. pigment blue 15:4 were replaced with
480.0 parts wt of C.I. pigment yellow 74. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 19
[0079] The inkjet ink of Composition Example 30 as shown in Tables
4 through 6 was prepared as in Comparative Example 7 except that
the 480.0 parts wt of C. I. pigment blue 15:4 were replaced with
480.0 parts wt of C. I. pigment yellow 74. In the compound of
Formula 1, R was a nonanol group, n was 7 and m was 4.
Comparative Example 20
[0080] The inkjet ink of Composition Example 31 as shown in Table 3
was prepared as in Example 8 except that instead of compound R
being a nonanol group, n being 7 and m being 4 in Formula 1 as in
Example 8, R was a hexanol group and PO-EO were added as blocks in
that order, with n being 4 and m being 4.
Comparative Example 21
[0081] The inkjet ink of Composition Example 40 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of
compound R being a nonanol group, n being 7 and m being 4 in
Formula 1 as in Example 8, R Was an eicosanol group and PO-EO were
added as blocks in that order, with n being 7 and m being 20.
Comparative Example 22
[0082] The inkjet ink of Composition Example 41 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of
compound R being a nonanol group, n being 7 and m being 4 in
Formula 1 as in Example 8, R was a nonanol group and PO-EO were
added as blocks in that order, with n being 2 and m being 8.
Comparative Example 23
[0083] The inkjet ink of Composition Example 42 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of
compound R being a nonanol group, n being 7 and m being 4 in
Formula 1 as in Example 8, R was a nonanol group and PO-EO were
added as blocks in that order, with n being 13 and m being 20.
Comparative Example 24
[0084] The inkjet ink of Composition Example 43 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of
compound R being a nonanol group, n being 7 and m being 4 in
Formula 1 as in Example 8, R was an eicosanol group and PO-EO were
added as blocks in that order, with n being 10 and m being 20.
Comparative Example 25
[0085] The inkjet ink of Composition Example 44 as shown in Tables
4 through 6 was prepared as in Example 8 except that instead of
compound R being a nonanol group, n being 7 and m being 4 in
Formula 1 as in Example 8, R was a heptanol group and PO-EO were
added as blocks in that order, with n being 10 and m being 20.
Evaluation Test 1
Method for Evaluating Plain Paper Color Development
[0086] The inkjet inks of Examples 1 through 20 and Comparative
Examples 1 through 24 were solid printed on Xerox P paper (Fuji
Xerox) using an inkjet printer (EM-930C, Seiko Epson) to obtain
test samples. The printing modes were paper: plain paper, print
quality: superfine, color correction: none, printing direction:
both directions. The OD values of each color were measured using a
GretagMacbeth Spectroscan SP50 (Gretag (U.S.)). The results are
shown in Tables 1 through 3 as OD values.
Evaluation Test 2
Method for Evaluating Glossiness
[0087] The inkjet inks of Examples 1 through 20 and Comparative
Examples 1 through 24 were solid printed on PM photographic paper
(Seiko Epson) with an inkjet printer (EM-930C, Seiko Epson) to
obtain test samples. The printing modes were paper: photo print
paper, print quality: photo, color correction: none, printing
direction: both directions. The 200 glossiness of the test samples
was measured with a gloss meter (HG-268, Suga Test Instruments).
The results are shown in Tables 1 through 3.
Evaluation Test 3
Method for Evaluating Dispersibility
[0088] The average particle diameters of the particles in the
inkjet inks of Examples 1 through 20 and Comparative Examples 1
through 24 were measured with a laser particle size analyzer
(Zetasizer 3000, Malvern (U.K.)). The results are shown in Tables 1
through 3.
Evaluation Test 4
Method for Evaluating Storage Stability
[0089] The initial viscosity and viscosity after 1 week's storage
at 70.degree. C. of the pigment dispersions for the inkjet inks of
Examples 1 through 20 and Comparative Examples 1 through 24 were
measured with a rolling ball viscometer (AMVn, Anton-Paar
(Germany)). The results for storage stability are given in Tables 1
through 3 as viscosity (mPa-s) after 1 week's storage at 70.degree.
C. divided by initial viscosity (mPa-s). The monomer composition,
polymerization initiator and pigment used in manufacturing the
inkjet ink and the inkjet ink composition are given in Tables 1
through 3.
TABLE-US-00001 TABLE 1 Ex 1 Ex 2 Ex 3 Ex 4 Ex 5 CE 1 CE 2 CE 3 BZA
483.0 483.0 483.0 483.0 483.0 483.0 483.0 483.0 AA 50.4 36.5 42.6
77.5 93.0 100.8 116.3 155.0 MAA -- 13.2 -- -- -- -- -- -- BPEH 5.6
5.6 5.6 5.6 5.6 5.6 5.6 5.6 PBk7 -- -- -- -- -- -- -- -- PB15: 4
480.0 480.0 480.0 480.0 480.0 480.0 480.0 480.0 PV19 -- -- -- -- --
-- -- -- PY74 -- -- -- -- -- -- -- -- Acid val. (mgKOH/g) 65 60 55
100 120 130 150 200 WAMW 34000 32000 48000 29000 34000 29000 34000
29000 Gloss (%) 71.3 68.9 70.9 76.8 74.2 74.2 77.1 76.5 Average
particle dia. 71 72 70 70 66 72 77 92 (nm) Stability 1.00 0.99 1.01
1.05 1.08 1.62 2.36 2.65 OD 1.20 1.20 1.21 1.17 1.01 0.95 0.91 0.93
CE 4 CE 5 CE 6 CE 7 Ex 6 Ex 7 CE 8 BZA 483.0 483.0 483.0 483.0
483.0 483.0 483.0 AA 50.4 36.5 50.4 23.3 50.4 36.5 100.8 MAA --
13.2 -- -- -- 13.2 -- BPEH 20.0 15.0 3.1 5.6 5.6 5.6 5.6 PBk7 -- --
-- -- 480.0 480.0 480.0 PB15: 4 480.0 480.0 480.0 480.0 -- -- --
PV19 -- -- -- -- -- -- -- PY74 -- -- -- -- -- -- -- Acid val.
(mgKOH/g) 65 60 65 30 65 60 130 WAMW 10000 18000 140000 33000 34000
32000 29000 Gloss (%) 42.1 40.5 25.4 30.1 50.6 52.1 44.3 Average
particle dia. 102 98 120 165 95 98 110 (nm) Stability 106.20 65.80
19.60 210.20 1.02 0.99 1.96 OD 1.11 1.11 1.06 1.20 1.30 1.28
0.98
TABLE-US-00002 TABLE 2 CE 9 CE 10 CE 11 Ex 8 Ex 9 CE 12 CE 13 CE 14
BZA 483.0 483.0 483.0 483.0 483.0 483.0 483.0 483.0 AA 36.5 50.4
23.3 50.4 36.5 100.8 36.5 50.4 MAA 13.2 -- -- -- 13.2 -- 13.2 --
BPEH 15.0 3.1 5.6 5.6 5.6 5.6 15.0 3.1 PBk7 480.0 480.0 480.0 -- --
-- -- -- PB15: 4 -- -- -- -- -- -- -- -- PV19 -- -- -- 480.0 480.0
480.0 480.0 480.0 PY74 -- -- -- -- -- -- -- -- Acid val. (mgKOH/g)
60 65 30 65 60 130 60 65 WAMW 18000 140000 33000 34000 32000 29000
18000 140000 Gloss (%) 45.8 31.2 50.6 68.2 74.6 70.3 62.9 34.6
Average particle dia. 130 156 146 71 72 71 89 110 (nm) Stability
40.30 32.10 162.30 1.02 1.00 1.01 35.20 53.20 OD 1.28 1.10 1.03
1.20 1.21 1.02 1.10 1.00 CE 15 Ex 10 Ex 11 CE 16 CE 17 CE 18 CE 19
BZA 483.0 483.0 483.0 483.0 483.0 483.0 483.0 AA 23.3 50.4 36.5
100.8 36.5 50.4 23.3 MAA -- -- 13.2 -- 13.2 -- -- BPEH 5.6 5.6 5.6
5.6 15.0 3.1 5.6 PBk7 -- -- -- -- -- -- -- PB15: 4 -- -- -- -- --
-- -- PV19 480.0 -- -- -- -- -- -- PY74 -- 480.0 480.0 480.0 480.0
480.0 480.0 Acid val. (mgKOH/g) 30 65 60 130 60 65 30 WAMW 33000
34000 32000 29000 18000 140000 33000 Gloss (%) 25.4 80.1 79.6 63.2
40.6 34.2 28.6 Average particle dia. 123 85 92 91 120 125 135 (nm)
Stability 165.30 1.01 0.99 1.01 32.50 58.60 154.30 OD 1.02 1.20
1.22 1.00 1.11 1.10 1.04
TABLE-US-00003 TABLE 3 Ex 12 Ex 13 Ex 14 Ex 15 Ex 16 Ex 17 Ex 18 Ex
19 BZA 483.0 483.0 483.0 483.0 483.0 483.0 483.0 483.0 AA 50.4 50.4
50.4 50.4 50.4 50.4 50.4 50.4 MAA -- -- -- -- -- -- -- -- BPEH 5.6
5.6 5.6 5.6 5.6 5.6 5.6 5.6 PBk7 -- -- -- -- -- -- -- -- PB15: 4 --
-- -- -- -- -- -- -- PV19 480.0 480.0 480.0 480.0 480.0 480.0 480.0
480.0 PY74 -- -- -- -- -- -- -- -- Acid val. (mgKOH/g) 65 65 65 65
65 65 65 65 WAMW 34000 34000 34000 34000 34000 34000 34000 34000
Gloss (%) 77.2 74.2 78.6 67.4 66.2 62.3 70.1 65.2 Average particle
dia. (nm) 71 71 71 71 71 71 71 71 Stability 1.00 1.00 1.00 1.01
1.01 1.00 1.01 1.01 OD 1.19 1.19 1.19 1.19 1.19 1.15 1.19 1.14 Ex
20 CE 20 CE 21 CE 22 CE 23 CE 24 CE 25 BZA 483.0 483.0 483.0 483.0
483.0 483.0 483.0 AA 50.4 50.4 50.4 50.4 50.4 50.4 50.4 MAA -- --
-- -- -- -- -- BPEH 5.6 5.6 5.6 5.6 5.6 5.6 5.6 PBk7 -- -- -- -- --
-- -- PB15: 4 -- -- -- -- -- -- -- PV19 480.0 480.0 480.0 480.0
480.0 480.0 480.0 PY74 -- -- -- -- -- -- -- Acid val. (mgKOH/g) 65
65 65 65 65 65 65 WAMW 34000 34000 34000 34000 34000 34000 34000
Gloss (%) 72.1 41.6 43.1 50.6 40.1 42.1 40.1 Average particle dia.
71 71 71 71 71 71 71 (nm) Stability 1.00 1.00 1.00 1.01 1.00 1.01
1.01 OD 1.19 1.19 1.06 1.10 1.05 1.02 1.00
TABLE-US-00004 TABLE 4 Composition Example Example/ 1 2 3 4 5 6 7 8
Comparative Example Ex 1 Ex 2 Ex 3 Ex 4 Ex 5 CE 1 CE 2 CE 3 PB 15:
4 4 4 4 4 4 4 4 4 PBk7 -- -- -- -- -- -- -- -- PV19 -- -- -- -- --
-- -- -- PY74 -- -- -- -- -- -- -- -- DEGmBE 0.2 0.2 0.2 0.2 0.2
0.2 0.2 0.2 TEGmBE 1 1 1 1 1 1 1 1 PGmBE -- -- -- -- -- -- -- --
DPGmBE 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 BEPD 0.1 0.1 0.1 0.1 0.1 0.1
0.1 0.1 Formula 1 added 1 1 1 1 1 1 1 1 Formula 1 R 9 9 9 9 9 9 9 9
Formula 1 n 7 7 7 7 7 7 7 7 Formula 1 m 4 4 4 4 4 4 4 4 Formula 1
R- R- R- R- R- R- R- R- Order of addition POEO POEO POEO POEO POEO
POEO POEO POEO Formula 1 Block Block Block Block Block Block Block
Block Form of addition 1,2-HD 4 4 4 4 4 4 4 4 Glycerin 15 15 15 15
15 15 15 15 TMP 7 7 7 7 7 7 7 7 Olefin E1010 0.1 0.1 0.1 0.1 0.1
0.1 0.1 0.1 Surfinol 104 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15
Ion-exchange water Trace Trace Trace Trace Trace Trace Trace Trace
Composition Example Example/ 9 10 11 12 13 14 15 Comparative
Example CE 4 CE 5 CE 6 CE 7 Ex 6 Ex 7 CE 8 PB 15: 4 4 4 4 4 -- --
-- PBk7 -- -- -- -- 5 5 5 PV19 -- -- -- -- -- -- -- PY74 -- -- --
-- -- -- -- DEGmBE 0.2 0.2 0.2 0.2 -- -- -- TEGmBE 1 1 1 1 2 3 4
PGmBE -- -- -- -- -- -- -- DPGmBE 0.1 0.1 0.1 0.1 -- -- -- BEPD 0.1
0.1 0.1 0.1 0.1 0.1 0.1 Formula 1 added 1 1 1 1 1 1 1 Formula 1 R 9
9 9 8 9 10 11 Formula 1 n 7 7 7 4 9 6 5 Formula 1 m 4 4 4 4 4 5 6
Formula 1 R- R- R- R- R- R- R- Order of addition POEO POEO POEO
POEO POEO POEO POEO Formula 1 Block Block Block Block Block Block
Block Form of addition 1,2-HD 4 4 4 4 3 3 3 Glycerin 15 15 15 15 10
10 10 TMP 7 7 7 7 4 4 4 Olefin E1010 0.1 0.1 0.1 0.1 0.1 0.1 0.1
Surfinol 104 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Ion-exchange water
Trace Trace Trace Trace Trace Trace Trace
TABLE-US-00005 TABLE 5 Composition Example Example/ 16 17 18 19 20
21 22 23 Comparative Example CE 9 CE 10 CE 11 Ex 8 Ex 9 CE 12 CE 13
CE 14 PB 15: 4 -- -- -- -- -- -- -- -- PBk7 5 5 5 -- -- -- -- --
PV19 -- -- -- 5 5 5 5 5 PY74 -- -- -- -- -- -- -- -- DEGmBE -- --
-- 0.3 0.3 0.3 0.3 0.3 TEGmBE 4 5 6 1 1 1 1 1 PGmBE -- -- -- -- --
-- -- -- DPGmBE -- -- -- -- -- -- -- -- BEPD 0.1 0.1 0.1 0.1 0.1
0.1 0.1 0.1 Formula 1 added 1 1 1 1 1 1 1 1 Formula 1 R 12 9 9 11 9
9 9 9 Formula 1 n 4 7 3 4 7 7 7 7 Formula 1 m 6 4 4 7 4 4 4 4
Formula 1 R- R- R- R- R- R- R- R- Order of addition POEO POEO POEO
EOPO POEO POEO POEO POEO Formula 1 Block Random Block Block Block
Block Block Block Form of addition 1,2-HD 3 3 3 4 4 4 4 4 Glycerin
10 10 10 10 10 10 10 10 TMP 4 4 4 5 5 5 5 5 Olefin E1010 0.1 0.1
0.1 -- -- -- -- -- Surfinol 104 0.15 0.15 0.15 0.15 0.15 0.15 0.15
0.15 Ion-exchange water Trace Trace Trace Trace Trace Trace Trace
Trace Composition Example Example/ 24 25 26 27 28 29 30 Comparative
Example CE 15 Ex 10 Ex 11 CE 16 CE 17 CE 18 CE 19 PB 15: 4 -- -- --
-- -- -- -- PBk7 -- -- -- -- -- -- -- PV19 5 -- -- -- -- -- -- PY74
-- 5 5 5 5 5 5 DEGmBE 0.3 -- -- -- -- -- -- TEGmBE 1 1 1 1 1 1 1
PGmBE -- 0.1 0.1 0.1 0.1 0.1 0.1 DPGmBE -- -- -- -- -- -- -- BEPD
0.1 0.1 0.1 0.1 0.1 0.1 0.1 Formula 1 added 1 1 1 1 1 1 1 Formula 1
R 9 9 9 9 9 9 9 Formula 1 n 7 7 7 7 7 7 7 Formula 1 m 4 4 4 4 4 4 4
Formula 1 R- R- R- R- R- R- R- Order of addition POEO POEO POEO
POEO POEO POEO POEO Formula 1 Block Block Block Block Block Block
Block Form of addition 1,2-HD 4 4 4 4 4 4 4 Glycerin 10 10 10 10 10
10 10 TMP 5 5 5 5 5 5 5 Olefin E1010 -- -- -- -- -- -- -- Surfinol
104 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Ion-exchange water Trace
Trace Trace Trace Trace Trace Trace
TABLE-US-00006 TABLE 6 Composition Example Example/ 31 32 33 34 35
36 37 38 Comparative Example Ex 12 Ex 13 Ex 14 Ex 15 Ex 16 Ex 17 Ex
18 Ex 19 PB 15: 4 -- -- -- -- -- -- -- -- PBk7 -- -- -- -- -- -- --
-- PV19 5 5 5 5 5 5 5 5 PY74 -- -- -- -- -- -- -- -- DEGmBE 0.3 0.3
0.3 0.3 0.3 0.3 0.3 0.3 TEGmBE 1 1 1 1 1 1 1 1 PGmBE -- -- -- -- --
-- -- -- DPGmBE -- -- -- -- -- -- -- -- BEPD 0.1 0.1 0.1 0.1 0.1
0.1 0.1 0.1 Formula 1 added 1 1 1 1 1 1 1 1 Formula 1 R 8 9 9 11 12
9 9 9 Formula 1 n 4 9 6 5 4 7 3 4 Formula 1 m 4 4 5 6 6 4 4 7
Formula 1 R- R- R- R- R- R- R- R- Order of addition POEO POEO POEO
POEO POEO POEO POEO EOPO Formula 1 Block Block Block Block Block
Random Block Block Form of addition 1,2-HD 4 4 4 4 4 4 4 4 Glycerin
10 10 10 10 10 10 10 10 TMP 5 5 5 5 5 5 5 5 Olefin E1010 -- -- --
-- -- -- -- -- Surfinol 104 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15
Ion-exchange water Trace Trace Trace Trace Trace Trace Trace Trace
Composition Example Example/ 39 40 41 42 43 44 45 Comparative
Example Ex 20 CE 20 CE 21 CE 22 CE 23 CE 24 CE 25 PB 15: 4 -- -- --
-- -- -- -- PBk7 -- -- -- -- -- -- -- PV19 5 5 5 5 5 5 5 PY74 -- --
-- -- -- -- -- DEGmBE 0.3 0.3 0.3 0.3 0.3 0.3 0.3 TEGmBE 1 1 1 1 1
1 1 PGmBE -- -- -- -- -- -- -- DPGmBE -- -- -- -- -- -- -- BEPD 0.1
0.1 0.1 0.1 0.1 0.1 0.1 Formula 1 added 1 1 1 1 1 1 1 Formula 1 R
12 6 20 9 9 20 7 Formula 1 n 7 4 7 2 13 10 10 Formula 1 m 6 4 20 8
20 20 20 Formula 1 R- R- R- R- R- R- R- Order of addition POEO POEO
POEO POEO POEO POEO POEO Formula 1 Block Block Block Block Block
Block Block Form of addition 1,2-HD 4 4 4 4 4 4 4 Glycerin 10 10 10
10 10 10 10 TMP 5 5 5 5 5 5 5 Olefin E1010 -- -- -- -- -- -- --
Surfinol 104 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Ion-exchange water
Trace Trace Trace Trace Trace Trace Trace
[0090] The abbreviations in Tables 1 through 3 and 4 through 6 are
defined as follows.
[0091] BZA Benzylacrylate
[0092] AA Acrylic acid
[0093] MAA Methacrylic acid
[0094] BPEH t-butylperoxy(2-ethylhexanoate)
[0095] PBk7: C.I. pigment black 7 (carbon black)
[0096] PB15:4: C.I. pigment blue 15:4 (copper phthalocyanine)
[0097] PV19: C.I. pigment violet 19 (quinacridone)
[0098] PY74: C.I. pigment yellow 74 (condensed azo)
[0099] DEGmBE: Diethylene glycol monobutyl ether
[0100] TEGmBE: Triethylene glycol monobutyl ether
[0101] PGmBE: Propylene glycol monobutyl ether
[0102] DPGmBE: Dipropylene glycol monobutyl ether
[0103] BEPD: 2-butyl-2-ethyl-1,3-propanediol 1,2-HD:
1,2-hexanediol
[0104] TMP: Trimethylolpropane
[0105] In Tables 1 through 3, BZA, AA, MAA, BPEH, PBk7, PB15:4,
PV19 and PY74 are given as parts by weight. Weight percentages for
each component are given in Tables 4 through 6. In Tables 4 through
6, R is the number of carbon atoms in the alkyl group, n is the
added molar number of the propyleneoxy PO, and m is the added molar
number of ethyleneoxy EO. The order of addition in Formula 1 is
R--POEO if the propyleneoxy PO is added first after the alkyl group
R and R-EOPO if the ethyleneoxy EO is added first after the alkyl
group R, and the form of addition in Formula 1 indicates whether
the propyleneoxy PO and ethyleneoxy EO are added to the alkyl group
R in blocks or randomly.
[0106] As shown by the results of Tables 1 through 3, good results
were obtained in all of Evaluation Tests 1 through 5 using the
inkjet inks of Examples 1 through 20, while good results were not
obtained in one or more of Evaluation Tests 1 through 5 using the
inkjet inks of Comparative Examples 1 through 24.
* * * * *